Skip Nav
Photography
50 Couple Moments to Capture at Your Wedding
Sex
The 29 Steamiest Movie Sex Scenes of All Time
Disney
These 30 Disney Princess Tattoos Are the Fairest of Them All

You Asked: Should I Tell My Best Friend I'm Dating Her Ex?

You Asked: Should I Tell My Best Friend I'm Dating Her Ex?

Dear Sugar,

My best friend and I had been close since the seventh grade. Seven months ago, I met her boyfriend. He was cute and funny and great to be with. In fact, we'd talk online every once and awhile. Unfortunately, a few months ago my friend and I had a huge falling out and we still aren't speaking. As of a month ago, her now ex-boyfriend and I started talking much more often and we have developed mutual feelings for each other. They still talk on occasion, but he hasn't said anything to her. Even though they broke up just before our falling out and although it was definitely mutual, I still feel guilty. Should we tell her?

—Crushing and Concerned Cassie

To see DearSugar's answer


Dear Crushing and Concerned in Cassie,

This is definitely a difficult situation. When it comes to dating a best friend's ex-boyfriend or crush, the code of rules is really complicated. Half the time we won't allow it, and the rest of the time we find a loophole. My general rule is don't do it unless you are absolutely in love and even that can get you in trouble, but at least it'll be worth it.

Since you and your friend are on the outs, she might see your relationship with her ex-boyfriend as a way of hurting her. Best friends often fight, but many are able to get past their differences in the end. Make sure that before you pursue a deeper relationship with this guy or decide to tell your friend, you're willing to potentially damage your friendship permanently.

Since she's still talking to her ex, it's likely that she'll find out about your relationship sooner than later. Your past fight might be forgivable, but sneaking around with her ex may not be. She'll be angry either way, but if you're direct and honest with her, it might be something you two can eventually work through. Either she'll forgive you or she won't, but at least you can sleep well knowing that you've been honest. Best of luck!

Source

Around The Web
Why You Should Date a Funny Guy
7-Day Sex Challenge
Signs You Were Meant to Break Up
Dating a Bookworm
Date Night Bucket List
Meaning of Roses: What the Number of Roses Means
Cute Love Comics by LoveByte

POPSUGAR, the #1 independent media and technology company for women. Where more than 75 million women go for original, inspirational content that feeds their passions and interests.

Join The Conversation
TFS TFS 8 years
not a very good friend are you.
bastille_75 bastille_75 8 years
Advah and jennifer76 are correct!!! To Advah - I would add #3 after you break you do not get the consolation prize of complete dominion over them and who they can and cannot date for the rest of their lives!!!! Also, to attempt to answer the question - you have to decide how much this friendship means to you. Do you wan to start to repair things with her - if so, you tell her now and even if she is initially mad bitter, etc., the friendship - if meant to recover - will. OR are you ready to accept the friendship as being over - b/c when she hears about this from anyone else including the guy - she will have what she'll perceive as the perfect excuse to write you off as a friend forever- rational or not. Good luck!!!
bastille_75 bastille_75 8 years
Advah and jennifer76 are correct!!! To Advah - I would add #3 after you break you do not get the consolation prize of complete dominion over them and who they can and cannot date for the rest of their lives!!!! Also, to attempt to answer the question - you have to decide how much this friendship means to you. Do you wan to start to repair things with her - if so, you tell her now and even if she is initially mad bitter, etc., the friendship - if meant to recover - will. OR are you ready to accept the friendship as being over - b/c when she hears about this from anyone else including the guy - she will have what she'll perceive as the perfect excuse to write you off as a friend forever- rational or not. Good luck!!!
Brandi2778232 Brandi2778232 8 years
Just let go of your friend, telling her would hurt her no matter what. That's my situation w/ex-bff. Her 15 years ago ex start dating me two years ago.... that's when we stop talking forever.
Jennifer777 Jennifer777 8 years
The question you need to ask yourself is: Do you ever expect to talk to your best friend again? If you don't then go ahead and date him, let her find out from him because you calling and telling her at this point would just be class-less... If you do then step away from the ex. He is off limits until you get the ok from her and that is gonna take the 2 of you mending your broken friendship first (and even then you might not get the ok...) Think hard about what you truly want for your future and who you really want in it... Good luck!
Ashlim Ashlim 8 years
My best friend hooked up with my ex within a week of our break-up. I felt especially betrayed because she knew he was horrible to me. When I confronted her about it she told me she didn't want to regret missing out on true love blah blah blah. It only lasted for 2 months. I tried to forgive her when she apologized to me and gave our friendship another try... but it just wasn't the same anymore. NYFashionista - I'm the same way! I see my friends' boyfriends as brothers too.
Ashlim Ashlim 8 years
My best friend hooked up with my ex within a week of our break-up. I felt especially betrayed because she knew he was horrible to me. When I confronted her about it she told me she didn't want to regret missing out on true love blah blah blah. It only lasted for 2 months. I tried to forgive her when she apologized to me and gave our friendship another try... but it just wasn't the same anymore. NYFashionista - I'm the same way! I see my friends' boyfriends as brothers too.
Martini-Rossi Martini-Rossi 8 years
I've never been in this situation (thanks God) but I think you should stick to the rule - Never date your best friend’s ex, whether your still friends or not. Since you feel guilty about it I believe that still means that you still care about your friend and have hopes of reconciling with her so dating her ex wouldn’t be a great idea. Remain friend with her ex and that it. If that too hard because of the chemistry then break all communication. You need to figure out what’s more important to you - a new bf? Or your old bff? Good luck and try not to get yourself in this kinda mess again. No one likes someone else's leftovers.
Martini-Rossi Martini-Rossi 8 years
I've never been in this situation (thanks God) but I think you should stick to the rule - Never date your best friend’s ex, whether your still friends or not.Since you feel guilty about it I believe that still means that you still care about your friend and have hopes of reconciling with her so dating her ex wouldn’t be a great idea.Remain friend with her ex and that it. If that too hard because of the chemistry then break all communication. You need to figure out what’s more important to you - a new bf? Or your old bff?Good luck and try not to get yourself in this kinda mess again. No one likes someone else's leftovers.
Korsgal Korsgal 8 years
Why are you dating him in the first place? I assume that you and your friend have a possibility of working thing out and becoming friends again. But now that you're dating this guy, I think it would be hard for the two of you to become friends again.
geebers geebers 8 years
Exactly - why would you deprive someone else of happiness for someone who YOU no LONGER are dating? That is terrible advice. However, the situation here is different because this isnt a girl dating her best friend's ex while they are still friends. If you and this girl are on the outs- there is zero chance of her forgiving you when you tell her "hey im sorry lets be friends again oh by the way im dating your ex". If you VALUE her friendship MORE than your relationship with this guy - I would take a break from him and try to rebuild it with her. If you and him are meant to be together and are in LOVE not lust -then trust me it will happen later on in time. If you become friends again - at least at this point you have done the right thing and can HONESTLY approach her and tell her you have feelings for him. Then it is her issue if she doesnt "approve" not yours. But if you dont care about her friendship - then you need to move on and just date this guy and realize you have no chance of being friends. Maybe if your friend is mature she will likely forgive and forget but I dont know this situation.
michelleannette michelleannette 8 years
tell her. she will find out eventually.the timing is unfortunate especially since you're not talking at the moment. maybe before you really get started with this guy you should patch things up with your friend. if he likes you, he'll understand that you need to focus on your friendship first.honestly, i wouldn't go for any of my friends exes. there is just too much possibility for conflict and to ruin a friendship. there are plenty of people to choose from.
michelleannette michelleannette 8 years
tell her. she will find out eventually. the timing is unfortunate especially since you're not talking at the moment. maybe before you really get started with this guy you should patch things up with your friend. if he likes you, he'll understand that you need to focus on your friendship first. honestly, i wouldn't go for any of my friends exes. there is just too much possibility for conflict and to ruin a friendship. there are plenty of people to choose from.
jennifer76 jennifer76 8 years
For the actual question at hand here, I don't know. That's a weird situation. Depending on what your friend is like, if you inform her that you're dating her ex, she may see that as an aggressive and hurtful thing not a compassionate thing. I really think this is a decision you have to make since only you know the people involved and the circumstances.For the topic this discussion has evolved into, I think the whole "cardinal rule" thing is ludicrous. If you actually care about your friends, why <em>wouldn't</em> you want them to be happy in their relationships? Why would you try to keep your friend away from someone they care about, simply because you're jealous. Jealousy is an ugly thing.And I have been in this situation but from the other side. My ex (my first love and an intense high school relationship) and one of my closest friends started dating a few months after he and I broke up. While I have to admit to twinges of jealousy, I did not feel "betrayed" in the least. He was a great guy and after a string of really crappy guys, she deserved a great guy. And she was a sweet girl and a lot of fun, and he deserved that too. I would have felt horrible stamping my feet and demanding they not see each other for the sake of my ego. Besides, I dated him while I was dating him. I don't own him forevermore.
jennifer76 jennifer76 8 years
For the actual question at hand here, I don't know. That's a weird situation. Depending on what your friend is like, if you inform her that you're dating her ex, she may see that as an aggressive and hurtful thing not a compassionate thing. I really think this is a decision you have to make since only you know the people involved and the circumstances. For the topic this discussion has evolved into, I think the whole "cardinal rule" thing is ludicrous. If you actually care about your friends, why wouldn't you want them to be happy in their relationships? Why would you try to keep your friend away from someone they care about, simply because you're jealous. Jealousy is an ugly thing. And I have been in this situation but from the other side. My ex (my first love and an intense high school relationship) and one of my closest friends started dating a few months after he and I broke up. While I have to admit to twinges of jealousy, I did not feel "betrayed" in the least. He was a great guy and after a string of really crappy guys, she deserved a great guy. And she was a sweet girl and a lot of fun, and he deserved that too. I would have felt horrible stamping my feet and demanding they not see each other for the sake of my ego. Besides, I dated him while I was dating him. I don't own him forevermore.
NYFashionista NYFashionista 8 years
I have to admit, I've always found it strange when best friends date each others' exes. I think for me, when I meet my best friend's boyfriend (a best friend who I consider as close to me as a SISTER- and I know many other women are like this) I immediately see her boyfriend as a brother...lol I would never or could never date anyone who I considered to be like a brother. So there you have it. That's my "rule". It works perfectly.
7kimba7 7kimba7 8 years
She will probably find out, since it's a small world. And even if you broke it off with him, she would eventually find out anyway. I think your friendship with her will be done because after all, you had a falling out MONTHS ago and haven't spoken. I think you should enjoy your boyfriend and not worry about your ex-friend, because that is spilled milk as far as I am concerned. You can't change what happened, and even if you stopped it now, it still happened in the first place.
7kimba7 7kimba7 8 years
She will probably find out, since it's a small world. And even if you broke it off with him, she would eventually find out anyway. I think your friendship with her will be done because after all, you had a falling out MONTHS ago and haven't spoken.I think you should enjoy your boyfriend and not worry about your ex-friend, because that is spilled milk as far as I am concerned. You can't change what happened, and even if you stopped it now, it still happened in the first place.
erratic-assassin erratic-assassin 8 years
I'm engaged to my bf's ex as well...when he approached me it had been a year since they stopped seeing each other. He knew and I knew that if we were going to embark on this journey, it would be for love or nothing. 2 months later we moved in and now we're getting married in August.I'm with you on this one LovelyLady. I dont believe in rules. They make me cringe. This chick may lose a friend, but who cares? I knew LOTS of people since grade school and now I don't speak to any of them today. Has it affected my life? NO. Enjoy your relationship and be happy. And piss on everything else. To those who say KARMA will haunt me, TRUST ME: THIS IS MY KARMA IN RETURN. I deserve this!
erratic-assassin erratic-assassin 8 years
I'm engaged to my bf's ex as well...when he approached me it had been a year since they stopped seeing each other. He knew and I knew that if we were going to embark on this journey, it would be for love or nothing. 2 months later we moved in and now we're getting married in August. I'm with you on this one LovelyLady. I dont believe in rules. They make me cringe. This chick may lose a friend, but who cares? I knew LOTS of people since grade school and now I don't speak to any of them today. Has it affected my life? NO. Enjoy your relationship and be happy. And piss on everything else. To those who say KARMA will haunt me, TRUST ME: THIS IS MY KARMA IN RETURN. I deserve this!
Advah Advah 8 years
Thanks for your post Pop, you said very clearly what I couldn't really explain in my post. :)I don't know why the replies in this thread bother me so much, I think I really can't understand why everyone explains it as a "rule". Again, I understand it will probably hurt her friend very badly. But if she decides not to stay with that guy to save her friendship, then she'll be hurt too. I wouldn't say that's a great definition of friendship..
Advah Advah 8 years
Thanks for your post Pop, you said very clearly what I couldn't really explain in my post. :) I don't know why the replies in this thread bother me so much, I think I really can't understand why everyone explains it as a "rule". Again, I understand it will probably hurt her friend very badly. But if she decides not to stay with that guy to save her friendship, then she'll be hurt too. I wouldn't say that's a great definition of friendship..
popgoestheworld popgoestheworld 8 years
I think this is "okay", and it's not because I've done it... I've had it "done" to me. The difference? My friend approached me and asked permission. I had moved on, he was a GREAT guy (still is), and she was a GREAT gal (still is). So I told them to go for it! I'm sure it would have been different if he'd dumped me and I was still reeling. But in this case it wasn't an issue at all. It didn't work out between the two of them, but I never felt anger at her, or him, for falling for eachother. And if it happened to me again, and this time it hurt more? Well too bad for me. Hurt feelings suck, but it's not like once you date a man you own him for the rest of your life.
popgoestheworld popgoestheworld 8 years
I think this is "okay", and it's not because I've done it... I've had it "done" to me.The difference? My friend approached me and asked permission. I had moved on, he was a GREAT guy (still is), and she was a GREAT gal (still is). So I told them to go for it! I'm sure it would have been different if he'd dumped me and I was still reeling. But in this case it wasn't an issue at all.It didn't work out between the two of them, but I never felt anger at her, or him, for falling for eachother.And if it happened to me again, and this time it hurt more? Well too bad for me. Hurt feelings suck, but it's not like once you date a man you own him for the rest of your life.
Kristinh1012 Kristinh1012 8 years
You don't even talk to her anymore. Why would you tell her? I don't get it? If you tell her it will look like you are just trying to be a b*tch and rub it in her face that you are with her ex. More than likely she probably really won't want to talk to you after that.
Latest Love
X